7 Activities To Enjoy In The Maryland City Of Annapolis

Mar 11, 2026 By Juliana Daniel

Annapolis, one of our favorite East Coast destinations, sometimes needs to be more appreciated in favor of bigger cities like Baltimore and Washington, DC. However, Annapolis, Maryland, offers a wide variety of exciting attractions. It's the picture-perfect capital city, a seaside getaway, and a bustling town. Everything from sightseeing to wine tasting to sailing the Chesapeake Bay is available, and there's much more. Here are some of our top picks for urban entertainment.


Take A Tour On A Trolley

Maryland's capital city has much more to offer than just the shops and restaurants on Main Street. Taking a trolley tour will let you see and understand this charming area in a new light. In that short time, you will be driven through some of the most beautiful structures in the area and given a brief overview of 350 years of history. The Naval Academy, as well as several historic homes, as well as mansions from the colonial era, as well as scenic vistas of the Severn River will all be in view. To see a lot of the city in a short amount of time while also being kind to your feet, a trolley tour ranks high on our list of things to do in Annapolis.


Explore The William Paca House

William Paca would have been the governor of Maryland in the 1780s in addition to being one of the state's four signers of The Declaration of Independence. His mansion, built in the 1760s, is today recognized as one of Annapolis' top tourist attractions. Careful excavations and the careful examination of ancient artwork have led to a meticulous restoration of the Paca House. On a sunny day, it's well worth your time to see the home, summer cottage, and two acres of formal gardens. We liked ascending to the summer house's loft for a bird's-eye view of the land and seeing how the wealthy had lived in the years leading up to the American Revolution.


Explore The Maryland State House

Annapolis is home to the nation's oldest state house, currently in active use by its legislature. Not only did significant events that shaped the country take place there, but it also served as the nation's capital for over a year between 1783 and 1784. It was at Maryland State House that George Washington resigned as head of the Continental Army as well as ratified the Treaty of Paris. Washington had intended to retire from public life, but things didn't work out that way. You may see old George in his finery and make your intentions clear if you go to the Old Senate Chamber today. The first home of George Washington is shown as well. Every history buff should make the short trip to see the State House.


Visit Great Frogs Winery And Schedule A Tasting

Fabulous Frogs Winery is a great spot to spend a day if you're looking for something to do in Annapolis outside the city. Founded in 1999 on what was formerly a tobacco farm, the winery makes use of the area's sandy soil to cultivate French Bordeaux varietals. Inside the end, the grapes become over a dozen wines, including white, rose, and red varietals and mixes.


Go To The Banneker-Douglass Museum

The Banneker-Douglass Museum, housed in a converted church, is the state's official museum of African American history. It was named within a week after Frederick Douglass, who was an anti-slavery activist after escaping from his enslaver, and Benjamin Banneker, a scientist as well as the writer. From Harriet Tubman, who helped guide enslaved people to freedom via the Underground Railroad, to Thurgood Marshall, the first African-American justice of the United States Supreme Court, the lives and achievements of notable Black Marylanders are highlighted in this museum. The state's Black cultural heritage may be explored by tourists interested in the African American community's history, culture, and contributions. Despite its modest size, this museum packs a powerful educational punch.


Stay At The Hotel By The Water

Annapolis has just one waterfront hotel, namely Annapolis Waterfront Hotel, which is ironic given the city's attractiveness. It is at a tranquil spot along the port, perfect for people watching sailboats and yachts come and go. The rooms on the upper floors take their design cues from the waterfront location and provide stunning views of the city or Spa Creek. The downstairs eatery and bar are Pusser's Caribbean Grille, a spinoff of the original establishment that first gained fame in the British Virgin Islands, thousands of miles to the south. Get yourself a drink, including painkillers, and prepare for a fun night out.


Take The Bridge To Eastport

Eastport may be found right after crossing the Spa Creek Bridge. As the locals will quickly remind you, Eastport is officially known as the "Maritime Republic of Eastport." The "Republic" was established in 1998 when the drawbridge between Eastport and downtown Annapolis was temporarily closed. It possesses its flag, sailing club, as well as community identity. A yearly tug-of-war known as "Slaughter Across the Water" brings forth this spirit of cooperation between the two sides. Enjoy wonderful waterfront eating year-round at Eastport's Boatyard Bar & Grill. Join the victors of the Wednesday Night boat races on the Chesapeake Bay as they celebrate their victories in the summer. Plus, the view of downtown and the Naval Academy from this side of the ocean is unrivaled.


Conclusion

Stop visiting America's Sailing Capital while you're in Maryland. With its location on the Chesapeake Bay, this city is a popular destination for watersports such as sailing, crabbing, and other water-based recreation. Even though water play is fun, there is a wider variety of activities to choose from. Many museums, parks, and hiking paths highlight Annapolis' rich history.

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